Using iPad or Windows at work. Which is better and why? What apps do you use?

Portable data on an un-encrypted device is a bad idea. While this may be allowed you will need to become intimately familiar with a few regulations (see below). Additionally, when your Soldiers sign their "Soldier's Privacy Act Statement" allowing you to maintain the SSN and personnel info in your Leader's Book you will need to amend the statement to include digital files on a personal device. Keep in mind that even after deleting a file a digital copy remains on the device and may be retrieved using the right software.

Read:
DA Pam 25-403 Guide to Record Keeping in the Army
AR 340–21 The Army Privacy Program
AR 380–5 Department of the Army Information Security Program
DA Pam 25–51 The Army Privacy Program–System of Records Notices and Exemption Rules

Well, if it's work, then your work should provide the tools for you to succeed. Many places/Service IPad's are a no go, and no wireless is the norm. Semper FI

I use both platforms at home, windows for gaming, and serious paper writing, iPad and iPhone for mobility. However, I strongly believe OSX is suitable for professional office applications.